You already know it's illegal. Only you can tell us if the risk is worth it. BTW IMHO the point of vacation is vacation. If you are working during your "vacation" then you are doing it wrong.

It is illegal, and if you are caught you will face tax evasion and possibly fraud charges. The UK has left the EU.

What % of the 60 or so days you’ll be in Italy do you plan to spend working? A few hours here and there during your trip is probably not a big deal. You should be prepared to show Immigration proof of your accommodation and insurance for your trip, a return or onward ticket, and that you have enough money for your stay. Note that your host must inform the local immigration office (questura) in writing within 48 hours after you arrive at their property, I don’t know if that could cause you or them a problem if they think you are working rather than visiting.

@o.m What is this based on? The charges mentioned seem completely fanciful, the real risk is some sort of immigration violation.

@Relaxed, he'd have to pay INPS as a freelancer, and as an employee his employer would have to. I presume the OP plans to do neither. The OP would be within the time window for his stay in Italy, it would be activities which are unacceptable under the terms of his stay.

@o.m. He is also not supposed to work at all, isn't that a more fundamental problem? For local employers, there is a special criminal for that (irregular or unreported work). Again, what's your earlier comment based on?

Oh wow. Ok i didn't know i could face charges, i honestly thought at worst it would be immigration issues. And i also kept reading through other sources it's really hard to enforce unless you literally just tell them you're working and drop yourself in it. So yeah it's definitely not worth it then.

@PeterM I never thought it was 'solidly' illegal, only that i saw some other posts on here that did mention it was technically illegal for other cases not involving Italy. So it's hard to know what to make of it all when you're researching this, that's why i wanted to ask in my specific case :)

@Luke97 "technically illegal" is still "illegal" There is no wiggle room. That the authorities may or may not be aware of your activities doesn't change the legality of them.

Ok thanks bud @PeterM

@Luke97 Citizenship of the person involved is also important aspect to this question. An EU citizen, resident in the UK, won't have immigration problems.

@Relaxed, I get the feeling that you're focussing on the most serious charge and neglecting the lesser included charges. But the prosecution may "throw the book at him" and charge immigration and all the rest. It is welfare fraud to get something one shouldn't get, and it is welfare fraud not to pay the statutory contributions.

Also guys, i will be getting paid into a UK bank account and be paying taxes in the UK. This isn't a freelancing sorta deal. I'm not sure if this matters at all.

@Luke97, it does matter. Your account may be in the UK, but your employer should inform the Italian authorities that someone living in Italy is working for that UK company.

@o.m. I am focussing on what happens in reality, you're yet to provide any basis for your comments.

@Luke97 Consider this: what if you work for a local restaurant and get paid on a bank account in the UK, do you think you would be exempted from all the local rules? In fact, in the EU it is actually possible (if controversial) to be employed by a company in another EU country. Minimal wage and taxes would be paid in your country of origin but mandatory contributions to health insurances and the like have to be paid in the country where you work.

The difference in your case is that your client/job is not really related to the local market, not the fact you're getting your salary paid in the UK.

That's where i was getting confused tbh @Relaxed. I'm someone who is really uneducated on this topic and i think for my case it appeared to be a bit of a grey area. I've spoken to a few people in my industry while looking into this and some have said they have worked remote on a tourist visa. I guess if word gets out then they are going to prison for fraud and tax evasion.

Another grey area to me is what constitutes working in my case? If i just respond to an email while I'm there am i going to get arrested and charged?

Whilst some of the comments here are technically correct, I suspect that the reason they have been posted as a comment and not as an answer is because the authors know just how severely the answer will be challenged. The long and short of it is, as an IT worker, logging in to push some git commits or make front-end changes, no one in Italy will ever know you are working and nothing will happen to you. You take your own risks obviously. If commenters feel otherwise then they need to write full answers and stop using the comment box to push opinions and vague legal threats.

@Venture2099: no one will know until the nice lady you talked to in your accommodation, or the girl you tried to impress at a local bar, calls the police to report you. I have seen that countless times while living in Asia, from digital nomads doing their regular IT jobs from their residence on the beach to young tourists teaching their language a few hours a week to help pay their trip.

Having spent considerable amount of time in Italy I simply do not believe that someone calling the police to report an IT worker will be investigated. I think it is complete hyperbole and if you truly believe that, then write an answer instead of a comment. We are not referring to Chiang Mi or other Asian locations.

@Venture2099 All it takes is something like the OP casually mentioning to the Italian immigration authorities that he will be working while on a tourist visa and he is in trouble. No need for someone to report him.

@Relaxed, you are right, it is the employer who gets fined rather than the employee for INPS evasion.

@Venture2099, it is a firm policy on this board not to advocate illegal activity, even if enforcement is lax. The consequences of getting caught can be severe and last a long time.

@Luke97 Many people have done it, the likelihood of getting caught is very low and I don't think it's a focus for enforcement in Italy (unlike the UK). That doesn't mean it's legal or a grey area at all. Think of it as speeding on the motorway if you will, happens every day, you can easily avoid getting caught, it's clearly illegal, consequences are usually mild but can be serious.

@Luke97 - have you seen the amount of nations offering a free working Visa to UK citizens who are explicitly remote workers? Iceland, Montserrat, Grand Caymans, Aruba, Madeira

As long as you have a salary and a remote job..you can live there for up to a year.